Recently, it has been proposed that Reissert compounds be synthesized to develop novel heterocyclic polymers for high performance applications (see H. W. Gibson et al., Amer. Chem. Soc., Polymer Preprints, 29(1), 154, 1988). Bis (Reissert compounds) have been synthesized in excellent yields by the use of a trimethylsilyl cyanide reagent and can be used to develop such polymers (see A. Pandya et al., Amer. Chem. Soc., Polymer Preprints, 30(1), 206, 1989). Several novel 4,4'-coupled bis-isoquinolines have also been synthesized (see H. W. Gibson et al., Amer. Chem. Soc., Polymer Preprints, 30(1), 208, 1989).
W. E. McEwen et al., in J. Org. Chem. 1980, 45, 1301-1308 discuss the synthetic uses of open-chain analogues of Reissert compounds by first preparing an aminonitrile by condensation of a primary amine with a cyanohydrin followed by reaction of the aminonitrile with an acid chloride to form the Reissert compound.
Chemical Abstracts, Vol. 87, 202161k reports on work by N. Voznesenskaya et al. in 1977 relating to the preparation of poly(phenyleneimidazolones) by polymerization of bis(alpha-aminonitriles) with aromatic dicarboxylic acid chlorides and subsequent cyclization of the prepared poly(alpha-cyanamides) by isomerization. The instant process has a number of differences over the process shown by Voznesenskaya et al: (1) the presence of aliphatic dialdehyde-derived alpha-aminonitriles; (2) the use of aliphatic diacid chlorides; and (3) the production of chemically modifiable copolymers, e.g., by copolymerization with polyester and polyamide precursors.